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Question

CH3OC2H5 and (CH3)3C−OCH3 are treated with hydroiodic acid. The fragments after reactions obtained are

A
CH3I+HOC2H5; (CH3)3CI+HOCH3
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B
CH3OH+C2H5I; (CH3)3CI+HOCH3
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C
CH3OH+C2H5I; (CH3)3COH+CH3I
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D
CH3I+C2H5OH; (CH3)3COH+CH3I
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Solution

The correct option is A CH3I+HOC2H5; (CH3)3CI+HOCH3
When mixed ethers are used, the alkyl iodide produced depends on the nature of alkyl groups. If one group is Me and the other a pri- or sec- alkyl group, then methyl iodide is produced. Here reaction occurs via SN2 mechanism and because of the steric effect of the larger group, I attacks the smaller (Me) group.
CH3OC2H5+HICH3I+C2H5OH

When the substrate is a methyl tert-alkyl ethers, the products are tert-RI and MeOH. Here reaction occurs by SN1 mechanism and formation of products is controlled by the stability of carbocation. Since carbocation stability order is
3o > 2o > 1o >+ CH3


Alkyl halide is always derived from tert-alkyl group.



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